Stadium: Center Court Round: 26 Ground: Grass
| ITF M15 Gaiba | 2021/06/09 16:15 | Alexander Hoogmartens v Federico Bertuccioli | 7-6,2-6,4-6 |
| ITF M15 Gaiba | 2021/06/08 08:45 | Lorenzo Bocchi v Federico Bertuccioli | 6-7,0-6 |
| ITF M15 Gaiba | 2021/06/07 12:30 | Patric Prinoth v Federico Bertuccioli | 4-6,4-6 |
| ITF M15 Antalya | 2021/05/02 06:00 | Jumpei Yamasaki v Federico Bertuccioli | 6-2,4-6,10-6 |
| ITF M15 Shymkent | 2021/04/15 03:55 | Federico Bertuccioli v Andrey Chepelev | 5-7,4-6 |
| ITF M15 Shymkent | 2021/04/14 04:00 | Vladyslav Manafov v Federico Bertuccioli | 4-6,4-6 |
| ITF M15 Shymkent | 2021/04/13 05:00 | Aleksei Khomich v Federico Bertuccioli | 2-6,4-6 |
| ITF M15 Shymkent | 2021/04/12 04:40 | Demid Gorbachev v Federico Bertuccioli | 0-6,0-6 |
| ITF M15 Gaiba | 2021/06/09 15:55 | Andrea Picchione v Tobias Simon | 5-7,7-6,5-7 |
| ITF M15 Sarajevo | 2021/06/02 10:40 | Tobias Simon v Federico Iannaccone | 1-6,3-6 |
| ITF M25 Meerbusch | 2021/04/15 13:25 | Tobias Simon v Tim Handel | 4-6,6-7 |
| ITF M25 Meerbusch | 2021/04/14 12:25 | Sebastian Prechtel v Tobias Simon | 5-7,6-3,3-6 |
| Challenger Lille | 2021/03/21 13:55 | Tobias Simon v Edan Leshem | 2-6,6-7 |
| ITF M15 Sharm El Sheikh | 2021/02/10 11:15 | Tobias Simon v Marek Gengel | 5-7,4-6 |
| ITF M15 Sharm El Sheikh | 2021/02/04 10:10 | Tobias Simon v Marko Tepavac | 4-6,2-6 |
| ITF M15 Sharm El Sheikh | 2021/02/03 12:50 | Tobias Simon v Remy Bertola | 6-2,6-4 |